311341-98-7

Upstream product

• 220249-56-9 tert-butyl(((3S,4R)-1-((4-methoxybenzyl)oxy)-4-methylhex-5-en-3-yl)oxy)dimethylsilane 

Downstream Products

• 541551-02-4 (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-hydroxy-6-methyl-octa-2,7-dienoic acid tert-butyl ester 
• 541551-03-5 (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester 
• 541551-05-7 (E)-(3S,10R,16S)-16-[(E)-(R)-3-(4-Benzoyl-phenyl)-1-methyl-allyl]-3-isobutyl-10-(4-methoxy-benzyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 541551-04-6 (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-((S)-2-{3-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester 
• 311342-00-4 tert-butyl (5S,6R,2E)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoyloxy]-6-methylocta-2,7-dienoate 
• 162600-54-6 cryptophycin-24 
• 311342-01-5 dephenyldesepoxyarenastatin A 
• 219606-86-7 tert-butyl (5S,6R)-5-[(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 
• 219606-79-8 tert-butyl (2E,5S,6R,7E)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-8-phenylocta-2,7-dienoate 
• 178977-57-6 tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate 
• 162473-78-1 desepoxyarenastatin A 

Relevant academic research and scientific papers

Total synthesis of cryptophycin-24 (arenastatin A) amenable to structural modifications in the C16 side chain

Two efficient protocols for the synthesis of tert-butyl (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)-oxy]-6-methyl-8-phenyl-2,7-octadie noate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of methyl 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1' methyl of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analogue, tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-phenyl compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analogue. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).

Synthesis and cytotoxicity studies of new cryptophycin analogues

Two analogues of cryptophycin were synthesized and biologically evaluated for their in-vitro cytotoxicities against several solid tumors and leukemia cell lines. The results revealed that both analogues exhibited a broad range of cytotoxic activity with observed IC50 values in the μM-range, and compound 4 was more effective than compound 3 in most assays studied.